DIPHENYL DISULFIDE Chemical Properties

Melting point:

58-60 °C (lit.)

Boiling point:

191-192 °C (15 mmHg)

Density 

1.353

refractive index 

1,441-1,444

FEMA 

3225 | PHENYL DISULFIDE

Flash point:

310°C

storage temp. 

Sealed in dry,Room Temperature

solubility 

xylene: soluble3%, clear, colorless to yellow

form 

Crystalline Solid

Specific Gravity

1.353

color 

White to off-white

Odor

at 0.10 % in propylene glycol. sulfurous earthy burnt

Odor Type

sulfurous

Water Solubility 

Insoluble in water.

JECFA Number

578

BRN 

639794

Stability:

Stable. Incompatible with strong oxidizing agents, strong bases.

InChIKey

GUUVPOWQJOLRAS-UHFFFAOYSA-N

LogP

4.41

CAS DataBase Reference

882-33-7(CAS DataBase Reference)

NIST Chemistry Reference

Disulfide, diphenyl(882-33-7)

EPA Substance Registry System

Diphenyl disulfide (882-33-7)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36/37/38-50/53

Safety Statements 

26-37/39-36-61-60

RIDADR 

UN 3335

WGK Germany 

3

RTECS 

SS6825000

F 

13

Hazard Note 

Irritant

TSCA 

T

HazardClass 

IRRITANT, STENCH

PackingGroup 

III

HS Code 

29093090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

DIPHENYL DISULFIDE Usage And Synthesis

Description

Diphenyl disulfide is a colorless crystalline material with the formula (C6H5S)2 and often abbreviated Ph2S2. It is most commonly utilized as a reagent for integration of a phenylthio functionality into molecules. The phenylthio group in the compound has a useful function due to the numerous of reaction that it can facilitate in organic chemistry. Phenysulfides, for instance, undergo oxidative elimination, producing alkenes under relatively mild, normal conditions. Also phenyl sulfides can serve as a source of carbon-centered radicals in radical reactions.
Diphenyl disulfide is usually synthesized by the oxidation of thiophenol:
2 PhSH + I2 → Ph2S2 + 2 HI

Reactions and Uses

With Alkenes
Ph2S2 adds cleanly to many dienes and alkenes upon catalysis by BF3.OMe2. The trifluoroacetoxysulfenylation of unsaturated esters, nitriles, amides, and carboxylic acids is possible with Ph2S2.
As a Source of Thiiyl Radicals
In the presence of radical initiators, upon thermolysis or photolysis, thiiyl radicals can be generated from PhSSPh. Therefore, the radicals generated add reversibly to alkynes and alkenes generating vinyl and alkyl radicals respectively (1).
Reduction
Ph2S2 undergoes reduction, which is a characteristic of disulfides. Hydride reagents such as super hydride and sodium borohydride can be used as reductants.
Ph2S2 + 2 M → 2 MSPh (M = Li, Na, K)

Chemical Properties

White to light yellow crystal.

Occurrence

Naturally occurring phytoalexin-like substan

Uses

Diphenyl disulfide is one of the most popular organic disulfides used in organic synthesis. It is used as a reagent for the α-phenylsulfenylation of carbonyl compounds. It participates in hydrothiolation of alkynes via amine-mediated single electron transfer mechanism. It is the hydrolysis product of dyfonate.

Definition

ChEBI: Diphenyl disulfide is a member of benzenes.

Preparation

By heating and passing a stream of air over an ammoniacal solution of thiophenol.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 35, p. 1770, 1987 DOI: 10.1248/cpb.35.1770
Tetrahedron Letters, 25, p. 703, 1984 DOI: 10.1016/S0040-4039(01)80004-6

Purification Methods

Crystallise the disulfide from MeOH. [Alberti et al. J Am Chem Soc 108 3024 1986]. Also crystallise it repeatedly from hot Et2O, then dry it in a vacuum at 30o over P2O5, fuse it under N2 and re-dry it; the whole procedure being repeated, with a final drying under a vacuum for 24hours. Alternatively, recrystallise it from hexane/EtOH solution. [Burkey & Griller J Am Chem Soc 107 246 1985, Beilstein 6 H 323, 6 IV 1560.]

DIPHENYL DISULFIDE(882-33-7)Related Product Information

• BENZENETHIOSULFONIC ACID S-PHENYL ESTER
• Bis(2-nitrophenyl) disulfide
• 2,2'-Diaminodiphenyl disulphide
• 4,4'-DICHLORODIPHENYL DISULFIDE
• 8,8'-DIQUINOLYL DISULFIDE
• Bis(3-nitrophenyl) disulfide
• DIPHENYL DISULFIDE
• 5,5′-Dithiobis(2-nitrobenzoic acid)
• BIS(2,4,5-TRICHLOROPHENYL) DISULFIDE
• 2,2'-Dithiobisbenzanilide
• DIPHENYL DISULFIDE-2,2'-DICARBOXYLIC ACID
• 6-HYDROXY-2-NAPHTHYL DISULFIDE
• BIS(4-METHOXYPHENYL) DISULPHIDE
• 4,4'-DINITRO DIPHENYL DISULFIDE
• P-TOLYL DISULFIDE
• 3,3',5,5'-TETRACHLORODIPHENYL DISULFIDE
• 2,2'',6,6''-TETRACHLORO DIPHENYL DISULFIDE
• 3,3'-DIFLUORO DIPHENYL DISULFIDE